Sodium Hydroxide → HCID 19389134, compound

HRID 1110242Notes

Reaction equation

HRID 1110242 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][N:5]([CH2:32][C:33]([O:35]C)=[O:34])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:7]=1.[OH-].[Na+]>O1CCOCC1.CO>[C:3]([CH2:4][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:7]=1)[CH2:32][C:33]([OH:35])=[O:34])([OH:37])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19018993HCID 19018993, compound

Product 1

HCID 19389134HCID 19389134, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.8 g N-(2-methoxy-2-oxoethyl)-N-[3-[(1-oxooctadecyl)amino]phenyl]glycine methyl ester and 2.4 ml of 6N NaOH in 30 ml of dioxane and 30 ml of methanol was heated to dissolve the solid and left at room temperature for 18 hours. The solid which precipitated was filtered, treated with 1N HCl and filtered again. Recrystallization from methanol-THF-water gave 1.35 g (79% yield, mp 135°-140°) of N-(carboxymethyl)-N-[3-[(1-oxooctadecyl)amino]phenyl]glycine.

Workup

  1. temperaturewas heated
  2. dissolutionto dissolve the solid
  3. customThe solid which precipitated
  4. filtrationwas filtered
  5. additiontreated with 1N HCl
  6. filtrationfiltered again
  7. customRecrystallization from methanol-THF-water

Sources & evidence

ORD record
ord-80ef4dee61ee4c069fb2ccb8d8ddb7b1
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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